A wooden pier extending into a clear blue sea with a sandy beach in the foreground and a cloudy sky above.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13
No exact matches found, but these alternatives could be just right

Recommended hotels in Upper Matecumbe Key

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,761 reviews)
"Beautiful resort! Very tropical vibes! I would definitely stay here again!"
United States
Alisha
The price is ₩209,330
₩313,449 total
includes taxes & fees
Sep 2 - Sep 3
Chesapeake Beach Resort
A courtyard with palm trees and flower beds, surrounded by buildings with balconies and a central entrance.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,417 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
The price is ₩206,489
₩333,647 total
includes taxes & fees
Sep 2 - Sep 3
Cheeca Lodge & Spa
A beachfront property with a staircase leading to a light blue building, palm trees, and a clear view of the ocean.

3. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Good location and great staff"
United States
adrian
The price is ₩165,191
₩224,823 total
includes taxes & fees
Aug 27 - Aug 28
La Jolla Resort
A resort with palm trees, a white building, and a sandy ground.

4. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,108 reviews)
"Staff and resort were amazing!"
United States
Chris
The price is ₩310,426
₩442,773 total
includes taxes & fees
Aug 31 - Sep 1
Islander Resort
A modern two-story beachfront property with balconies, a pool, and a sandy beach area.

5. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"I had an excellent stay at the resort. and look forward to returning!"
United States
Isabel
The price is ₩242,798
₩349,549 total
includes taxes & fees
Aug 31 - Sep 1
Pines & Palms Resort
A building facade with the text "Buzzy Plims" and a website address. There are two potted plants and a staircase leading up to the entrance.

6. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (729 reviews)
"Great place to stay rooms were really nice nice boat ramp plenty of parking restaurants right down the street to eat at no complaints nice pool everybody was friendly room was ice cold from the air condition full kitchen nice balcony looking out over the ocean great stay"
United States
roger
The price is ₩142,186
₩182,070 total
includes taxes & fees
Sep 1 - Sep 2
Breezy Palms Resort
An aerial view of a resort with a swimming pool, palm trees, and a dock.

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,294 reviews)
"Best place to stay !!"
United States
David A
The price is ₩232,924
₩363,386 total
includes taxes & fees
Aug 25 - Aug 26
Amara Cay Resort
A building with a green roof and a sign that reads "Hadley House Oceanfront Resort."

8. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,013 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
The price is ₩151,956
₩216,170 total
includes taxes & fees
Sep 7 - Sep 8
Hadley Resort and Marina
A resort with a central swimming pool surrounded by palm trees and a view of the ocean.

9. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (457 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
The price is ₩325,532
₩459,767 total
includes taxes & fees
Aug 31 - Sep 1
Bayside Villas by Islander Resort
A row of colorful beach huts with palm trees in the background.

10. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,011 reviews)
"Great place to stay!"
United States
Brianne
The price is ₩214,214
₩342,338 total
includes taxes & fees
Aug 25 - Aug 26
La Siesta Resort & Villas
A resort with multiple-story buildings, palm trees, and a well-maintained lawn.

11. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (80 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
The price is ₩498,899
₩647,633 total
includes taxes & fees
Aug 29 - Aug 30
The Islands of Islamorada
A two-story building with a balcony, surrounded by palm trees and a sandy ground.

12. Sands of Islamorada

Sands of Islamorada
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (414 reviews)
"Great place to stay!"
United States
Virginia
The price is ₩278,552
₩332,087 total
includes taxes & fees
Sep 17 - Sep 18
Sands of Islamorada
A two-story building with a covered porch and a pathway leading to it, surrounded by lush greenery and palm trees.

13. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (451 reviews)
"The hotel was in the mist of redoing it's landscaping by adding gaint palm trees and some new boat docks, but it didn't interfere with the overall feel of the place. We enjoyed the free paddle boards and pool. Its also located on a beautiful part of the Keys"
United States
Lois
The price is ₩229,493
₩273,771 total
includes taxes & fees
Sep 21 - Sep 22
Casa Morada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upper Matecumbe Key Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Amazing breakfast, clean room and very friendly staff."
Oleksandr 5-night trip
Posted 7 hours ago
Chesapeake Beach Resort

Find out more about Upper Matecumbe Key

Upper Matecumbe Key Cabin Rentals information

Number of reviews
7,337
Accommodation
0 Cabin Rentals
Lowest Price
₩182,070
Highest Price
₩647,633

Frequently asked questions

Are there cheap cabins in Upper Matecumbe Key?
Whether you want to stay steps from the water or on the top of a mountain, we have an awesome variety of cheap cabins in Upper Matecumbe Key to suit your budget and taste. Priced from ₩182,070 to ₩647,633 per night, your ideal cabin is waiting right here. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the highest-rated cabins in Upper Matecumbe Key?
Expedia cabin travelers just keep coming back to Cabin - Sand Is The New Snow - New 4bedroom W. This top pick features a host of handy amenities including a private pool and a deck. It won't take you very long to see why Historic, Dog - Friendly Cottage In The Heart Of Key West W is also popular with vacationers. Conveniences such as a patio and a deck will help make your stay nice and comfortable.
Why should I book a cabin in Upper Matecumbe Key?
Affordability, outdoor attractions, rustic charm — there are countless great reasons to book an Upper Matecumbe Key cabin. Escape the noisy concrete jungle and wake up to the beautiful sounds of Mother Nature. There's so much adventure just around the corner too. Whether you're taking a break with friends, family or your partner, you'll find the perfect rental cabin on Expedia.
What are the top nature cabins in Upper Matecumbe Key?
Spend a few nights at Cabin - Sand Is The New Snow - New 4bedroom W and you'll be surrounded by nature. Amenities like a private pool and a deck help make this river cabin in Upper Matecumbe Key a top option. Historic, Dog - Friendly Cottage In The Heart Of Key West W is another place where you can escape the hustle and bustle and catch a few mindful moments by the water. Some of the conveniences here include a patio and a deck.